


Five Sexual Misadventures and One Averted One

by theaeblackthorn



Category: Teen Wolf (TV)
Genre: Awkward Sexual Situations, Bad Sex, Bottom Derek Hale, Come Shot, Established Relationship, Fluff, Hand Jobs, M/M
Language: English
Status: Completed
Published: 2013-01-22
Updated: 2013-01-22
Packaged: 2017-11-26 10:12:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,852
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/649472
Author URL: https://archiveofourown.org/users/theaeblackthorn/pseuds/theaeblackthorn
Summary: <blockquote class="userstuff">
              <p>Stiles has been wheedling Derek into trying novelty condoms for <i>ages</i> and eventually he agrees.</p><p>"You're wearing it, though," Derek says, eyeing the box of 'Fire & Ice' condoms dubiously.</p><p>Stiles nods. "That's fine by me. Look it says <i>warming and tingling sensations to both partners</i>. How awesome does that sound?"</p><p>Derek's still eyeing the box dubiously. "I'm not a hundred percent I want 'fire' anything in my ass."</p><p>"It'll be fun," Stiles cajoles. Famous last words.</p>
            </blockquote>





	Five Sexual Misadventures and One Averted One

**Author's Note:**

  * For [Slumber](https://archiveofourown.org/users/Slumber/gifts).



> Everytime I try to write a Stiles/Derek sex scene, I get the overwhelming urge to make it end hilariously badly. I usually end up writing them, then deleting them and writing a more serious sex scene. I also can't help but be rambly about things. So, my beta challenged me to write all those atrocious sex scenes, and make it in total under 5k. Eeek.
> 
> One of these is totally based on a user on bad_sex over on lj. I knew I wanted a sex toy/something one, and well. Their horrific story was too much to resist, and it turns out they weren't the only ones who had issues with that brand of condom.
> 
> Posting unbeta'd because it's for my bb beta, and I can't make her beta her own fic! XD
> 
> ETA: MASSIVE THANKS TO CHRISTA FOR SAYING, 'WHERE IS SAS SAS WRITE A FIC OF DEREK AND STILES EATING RIBS TOGETHER AND IT'S SUPER MESSY' it's a bit of a fake out on that one, but still there! XD

Derek is Stiles's first. Which, okay. So it's not that surprising, not really. (You've met Stiles, right?) And Stiles is Derek's first in… a long time; a very long time. (Her name is _never_ to be mentioned.) At the start it's a horrible mess of Stiles not being able to focus, no-one knowing where to put their elbow (no seriously, _where_ ) and both of them coming too soon.

But that's okay, because Stiles won't let himself be daunted by awkwardness and embarrassment, he is the _king_ of awkwardness and embarrassment. He makes them his bitch. And Derek… Derek is oddly determined when he sets his mind to something. They practice _lots_ and they get better. A lot better.

But not quite perfect, not yet.

*

One.

Stiles always panics when they have his dad over. Even though they're not doing anything illegal _now_ , Stiles gets that guilty kid feeling and... yeah. It wouldn't be a problem except they have his dad over every Sunday for dinner these days.

The meal goes really well, Derek's the main cook in the house, but Stiles is his glamorous kitchen assistant and gets assigned chopping duty. They make five-bean chilli and all in all a success. His dad never has to know it's soya mince in it. Never.

It's late when he finally leaves and Derek and Stiles head straight to bed. Stiles is most definitely in the mood, Derek was charming and sociable, his chilli was fucking delicious, so yeah, a certain alpha has something excellent coming his way. Pardon the pun.

Stiles gets Derek leaning on the edge of the bed, naked for him to enjoy.

"So, _man of the house_ are you ready for your reward?" Stiles asks, crawling onto the bed and dropping the bottle of lube next to Derek.

Derek's eyes briefly flit down to it and a slow grin spreads across his face. Yeah, he knows what's coming.

Stiles leans forward and kisses Derek, short and sweet. He's got better things to do with his mouth. He kisses his way down Derek's chest, not stopping until he reaches Derek's cock. It's already already half-hard... Stiles loves to know he's appreciated.

Stiles loves Derek's cock. No seriously. It might not be the most aesthetically pleasing sight for _delicate_ eyes, but his eyes aren't fucking delicate and he thinks it looks perfect. He loves all of it, from the foreskin he likes to play with to the thick vein on the underside he loves to trace his tongue against. He loves what he can do to it, he loves what it can do to _him_.

Derek has already let himself slip down the headboard, so his feet are flat on the bed and his knees falling lazily apart. Stiles reaches over and grabs the lube, putting some in his hands to warm it up. He coats two fingers and leans forward.

"Lie back, and close your eyes," he commands and feels a thrill run through him as Derek follows his command exactly.

Stiles waits, half of this is the anticipation. Slowly he crawls forward bringing his head to rest near the tip of Derek's now hard cock. He lets his breath ghost over it and sees Derek's abdominal muscles clench up. He licks his lips, knowing Derek will be hyper-focused on him, his other senses enhanced with his eyes closed.

Patient isn't a word most people would use to describe Stiles, but, when it's part of a devious plan... Stiles can be as patient as a saint.

He darts his tongue out for a taste of Derek whilst letting his hands drop down, to open Derek's cheeks. Derek's cock is hard and warm against his tongue, Derek moans in frustration as Stiles laps at the head with little kitten licks.

He pulls back. He's still got Derek spread open before him and he finally circles a finger and pushes slowly inside. He doesn't waste time going slow quickly thrusting in. He barely waits a second before he takes Derek's cock in his other hand, holding him steady as wraps his lips around the head.

Stiles stares up through his lashes at Derek. He only gets a moment to appreciate Derek with all of his senses, the taste of his cock, the feel of him under his fingers, the musky smell, the drawn out groans, the ecstatic look on his--

"Stiles, oh god, Stiles _stop_!" Derek says, pulling sharply away from Stiles and nearly kneeing him in the face.

Stiles sits back out of his way, his fingers cool as the air dries them. Derek is grabbing at his dick and hisses like something burn-- oops.

Before he can ask if it's the chilli from earlier Derek is running out of their bedroom, stark naked, towards the bathroom. Stiles follows and sees him jump in the shower.

"You should have scrubbed your hands more!" Derek complains. He's frantically soaping at his dick and ass.

Hey, that's not... "I did! I washed them in the sink!"

"You should have washed them better! Oh god it _burns_ , Stiles, it _burns_."

"Try running the cool on it then, not the hot!"

"I don't think chilli works like that. _Make it stop burning_."

"I _can't_."

Next time they have chilli, Derek doesn't ask Stiles to help with the chopping.

*

Two.

Stiles wakes up to a dry mouth and an itchy chest. He reaches down to scratch it and feels the dried come flake away. Ew. He's got to stop letting Derek cuddle him tight and fall asleep after they come. Even a wet flannel near the bed would be better than having to wash dried come out of his chest hair in the morning. (Stiles has _finally_ reached the point in his life where there are too many hairs on his chest to count. And by 'too many' Stiles means about twenty. Not that he's counted, damnit.)

He reaches over takes a sip of water from the glass on their bedside table. The sky is dark outside which means it can't be too late, he glances at his phone, it's only one AM. Hm... plenty of time for something more. Derek is sleeping face down, arms curled around his pillow and his face firmly hidden away from the world. The broad, naked expanse of Derek's back is facing Stiles and... yeah, he wants that.

(One day, when Derek is sleeping, Stiles is going to cockslap him because he really wants to. Today is not that day because that would make Derek grumpy and he really would quite like to have sex right now, not put up with a sourwolf.)

He leans over and starts kissing his way down Derek's back. Derek has moles, not as many as Stiles, not nearly, but they're faint and hidden, scattered across his back. Stiles traces a trail down, trying to spot them in the faint light the moon.

Derek moans slightly and shifts in his sleep. Stiles stills. He can't help but make a game of things, and this just changed into how long can he do this before Derek wakes up. When Derek has settled again he resumes, he licks and even runs the hint of his own stubble against a few of them. The sheets are just covering the top of Derek's ass so Stiles carefully pushes them out of the way.

If there is anything Stiles loves more than Derek's cock, it's his ass. No really. You have to see it to understand. It fills his jeans in a way that should be illegal, it's firm and round, with the lightest dusting of hair.

Stiles leans forward, he means to lick, he _really, really does_. But he can't resist, he nips, quick and maybe a little hard...okay, so it's hard.

What he isn't expecting is for Derek to yelp and buck up against him. Derek is close to the edge of the bed and it causes Derek to slide off the side taking the blankets and Stiles with him. There's a mad scramble and a blinding flash pain as Stiles smashes his head against the nightstand.

When they stop moving Stiles is laying on top of Derek, the sheets wrapped around their legs and pinning them in place and his head _really, really hurts_. It's throbbing and he can feel wetness in his eye like he's crying, but only in one eye?

He tries to open an eye to see what's going on but there's... fuck is that blood in his eye? His head really hurts.

"Stiles, what the fuck is happening? Why can I smell blood? What--" Derek is getting himself distressed.

"Jesus, fuck, my head hurts." Stiles holds a hand up to his forehead and feels it come away wet. From years of being with the 'wolves he's learnt the hard way that head wounds tend to bleed and look worse than they are, but it never hurts to be safe. "I think we need to go to the ER."

It's just their luck that Melissa is working that night, when they turn up with Stiles wearing a shirt too big for him, and Derek a shirt too small. She takes one look at them, the painfully embarrassed look on Derek's face and says, "I'm not even going to ask. Wait in cubicle two, I'll be in in a minute." 

Stiles gets three stitches and some pretty trippy painkillers. Maybe the cockslapping plan can wait a few months; he'll be better prepared next time.

*

Three.

Derek gives the best blow jobs, he has the perfect fucking lashes to look up at, and the _perfect_ face to come on. And chest... abs... back... fine, Stiles _really_ likes coming on Derek. Which works out pretty well, all things considered, because Derek likes to be covered in spunk.

What? Stiles is still a teenager, you know. (Just.)

Derek has got Stiles pinned against their bedroom door, that's as far as they made it before Derek just couldn't wait anymore. Derek's in one of his filthy tank tops and worn, tight black jeans that should be _illegal_. He calls them his 'about the house' clothes, Stiles calls them his hooker clothes.

Somehow Stiles has lost his shirt, but his jeans and boxers are on, just pushed halfway down his thighs. His hands are fisted tight in Derek's hair as Derek works his cock like a pro. It's all wet, tight suction and every now and then barest hint of teeth. Derek's stubble scratches against Stiles's inner thighs as he moves to mouth and suck at Stiles's balls.

Derek's hand is still wrapped around Stiles's cock, sliding up and down it made easy with all the spit he's left on it. Stiles tugs on Derek's hair, trying to pull him back, trying to tell him that he's close, so close and he's about to come--

Fuck, Derek pulls back just in time for Stiles to come all over his face. The first pulse hits Derek's straight in his open eye and it's fucking chaos from then. Derek is the only thing holding Stiles up and as the come hits he recoils back, letting go of Stiles who drops to the floor; still coming.

It's not like Stiles is a werewolf with a shitload of come, he's just a human, but every strand seems to land somewhere ridiculous on Derek: his ear, his nose, it's a fucking disaster. Stiles's ass hits the ground with a painful bump and Derek is falling over himself trying to get the come out of his eye. But he's just rubbing it in more.

"It burns, Stiles, it burns. _Motherfucker_. How did you even--" He sneezes and it sends a glob of come flying onto Stiles.

Derek's got this scowly look on his face, his eye is watering and he's still trying to get the come off him, he looks so fucking disgruntled. Like a cat that's just been dropped in a sink full of water. It's-- it's fucking hilarious.

Stiles starts laughing, he can't help himself and the more put out Derek looks the harder he keeps laughing.

"It's not funny," he says, squinting at Stiles with his one puffy eye.

"It kinda is, dude."

"I'm fucking a child."

Stiles doesn't dignify that with a response. He just laughs more. So he can be a bit of a dick sometimes, it's all part of his ~charm.

*

Four.

On principle Derek doesn't like condoms. He can't catch diseases and he's overly fond of come. Like, really overly fond of come. Stiles likes the stuff a bit more than your average person but shit, Derek _loves_ the stuff. Stiles first thought it was a wolf thing, but he's come to suspect it's just a Derek thing.

But anyway, Stiles has been wheedling Derek into trying novelty condoms for _ages_ and eventually he agrees.

"You're wearing it, though," Derek says, eyeing the box of 'Fire & Ice' condoms dubiously.

Stiles nods. "That's fine by me. Look it says _warming and tingling sensations to both partners_. How awesome does that sound?"

Derek's still eyeing the box dubiously. "I'm not a hundred percent I want 'fire' anything in my ass."

"It'll be fun," Stiles cajoles. Famous last words.

He preps Derek like normal with their boring non-flavoured, non-tingling lube (seriously, Stiles, do you have any idea what that other shit is like to enhanced senses? We're never using strawberry lube _ever_ again, I don't care if it smelled good).

Stiles rolls the condom on and is a little disappointed, he can't feel anything different from a regular one. He shrugs and thinks, 'maybe it takes a while to kick in.'

He slides in slow, he loves this moment the first push into Derek, feeling him tight around him. It's all slick heat that makes him want to push in straight to the hilt, but... they do this often, but not often enough. Derek's always so fucking tight, the first few times they tried with Stiles on top he barely got in before he came.

He's better these days, but he still has to take a moment when he's fully in. He waits for Derek to start pushing against him, until then he just holds still and touches Derek the way he likes to be touched.

They've known each other long enough, they've been fucking each other long enough, that there's not just 'sex' between them. There's 'Derek has had a shitty day and needs to be reminded that Stiles isn't going anywhere' sex, there's 'Stiles is tired of his position being questioned in the pack' sex, there's even, 'yay, it's Thursday' sex. ('Yay it's Thursday' sex is actually pretty fucking freaky.)

Stiles loves all of it, he loves Derek taking charge, he loves ordering Derek about, he loves being a pushy bottom as much as he loves being a passive top. He loves giving Derek what he wants. He loves Derek seeing his needs and giving Stiles what he wants. Pretty much he loves Derek, in any way, shape or form he can have him.

Stiles can feel it's time to start thrusting, Derek is making these fucking wrecked keening noises, and breathy moans (he'll deny it if you ever try and tell him he makes breathy moans, but he _does_ ). Derek's so into it, he's all eyes scrunched closed and rising up to meet every thrust and yeah, fuck it's good.

Except, there's a strange feeling on his dick like... it doesn't feel amazing, it doesn't hurt it's just... weird. He keeps fucking Derek, leans down to bite at his nipples and is rewarded by Derek arching into him.

The weird sensation doesn't go away, in fact, it's starting to get a little uncomfortable. But, Derek's really into it.

"Yeah, fuck that's angle's good. Don't stop-- Stiles, you're fucking perfect--"

Shit, it's starting to get really uncomfortable. Derek is close though, maybe he can just-- FUCK. It's burning, it's definitely burning, he needs this condom off him, like, _now_.

Stiles pulls out of Derek and is ripping the condom off as quick as he can. Fuck, the burning isn't stopping, at all. He needs to wash his dick, like, _right the fuck now_. He runs into the bathroom and the feel of the cool water on his dick is better, but it's not stopping it completely. Soap, maybe soap will stop it. He lathers up his dick, so soft now it's ridiculous and... yeah, okay, it's burning less.

He rests his head against the cool tiles of the bathroom and lets the water continue to flow over his dick. That... was horrible. Eventually he starts shivering from the cool water, he turns the shower off and dries himself down.

He walks back to their bedroom with the town wrapped tightly around his waist. Derek's finished himself off, which is kinda good because Stiles doesn't want to think about anything sex-related right now.

"No more novelty condoms?" Derek asks smugly. Like he knows the answer but just wants to make Stiles say it.

Stiles flops down on the bed next to him. "Fine, no more novelty condoms."

*

Five.

The fifth time they don't even make it to the sex part of the evening. Stiles demands a date for a change, but clearly neither of them thought it through properly because they end up at a ribs place and seriously. Ribs aren't sexy food.

That doesn't stop Stiles trying.

He ends up essentially fellating a bbq rib, and chokes on it. That's when Derek calls the night quits. 

 

*

Plus One.

It's not that they can't afford to turn up the heat, nor that the house is crappily insulated, it's just that it's really fucking cold outside. Like, _really cold_.

That pack have just left after spending the evening at the house: Allison snuggled into Scott's side for warmth and Lydia nestled in what Stiles likes to think of the beta-bundle (of Isaac, Erica and Boyd). Stiles was no different with Derek; huddling for warmth against the cold winter's evening.

Stiles is already in their bed, refusing to take off his hoodie because the bed is _cold_. Too cold to take off the hoodie and definitely too old to lose the sweatpants he's wearing. Derek comes out of their bathroom wearing nothing but a pair of boxers and Stiles is downright envious. He'd accept the bite right this second if it meant he could warm up. And he tells Derek so.

"I can think of far quicker ways to warm you up," Derek leers, in the endearing way that only Derek can.

"Dude, no, totally too cold for sex of any kind." Stiles snuggles under the blankets.

Derek climbs in the bed so they're laying face to face, heads propped on their own pillows.

"I bet I can change your mind," Derek says, and he sounds so _smug_ that Stiles wants him to be wrong. (Except for how he doesn't, because, well, _sex_.)

Stiles snorts and burrows deeper into his pillow. "Fine, prove it."

Derek grins, he's obviously been waiting for Stiles to say that. Derek shuffles forward in the bed until he's so close that if he were any close Stiles would go cross-eyed trying to hold his gaze.

He doesn't break eye-contact as he reaches over to caress Stiles's face. Stiles leans into the touch but that's all. Derek brings the hand that had been so soft, so chaste against his face and slowly drags his tongue over the palm, slicking it up. Oh, Stiles sees where this is going, so it's like _that_ is it?

Derek slips his hand down under the blankets and even though he can't _see_ where it goes, he can see the rustle of the bed covers and hear the slide of skin against fabric as Derek slips a hand into his boxers.

Stiles watches Derek as he slowly works himself. He can imagine what Derek's doing, he's watched him jerk off enough times. He goes slow at first, long strokes, down, and up, every now and then twisting up and over the head.

He bets there's precome gathering there already. Shit, Stiles wishes he could taste it, but he's not going to make this _that_ easy for Derek.

"That's all you've got?" He asks teasingly.

Derek grins, lazy and wide. "I'm in no rush," he says, but the sharp intake of breath tells Stiles that he's further along that he wants Stiles to know.

Derek leans forward until his hot breath is ghosting across Stiles's lips. He just holds himself there, licking at his lips and letting his eyes drift close.

Stiles fucking loves it when Derek bites at his lip, he wants that mouth... those lips bitten red already, shining and wet, practically _begging_ to be kissed.

It's been years but Stiles still can't believe he gets to have this, he gets to come home to this every day, he gets to fuck and be fucked by someone as fucking beautiful as Derek. And he's honest to god not just talking looks. Past the sourness, Derek is just like him. He's bitter, sarcastic, socially inept and he cares _way_ too much about those that matter to him. They're a pair and Stiles wouldn't have it any other way.

Stiles can't hold back any more, Derek's laying there, panting softly into Stiles's mouth as he works himself and he can see Derek bite his lip, trying to hold back from taking what he wants from Stiles.

This is a game Derek wants to win, and fuck it, Stiles wants Derek to win too. He leans forward and takes those lips. He kisses Derek like he want to fuck him, thrusts his tongue in and out, sucking and licking and owning that kiss.

Stiles can't help it now he's given in, he moves forward until every movement of Derek's hand bumps up against Stiles. He moves his own hand down to join Derek's and feels Derek flinch.

"Fuck your hands are cold," he whispers, close against Stiles's mouth.

Stiles chuckles, low and breathy. "I told you I was cold, dude."

Derek pulls Stiles's hand up until it sits nestled in his armpit. They don't stop kissing, but Derek does slow his pace some.

Stiles is hard, but he can wait. He wiggles his fingers trying to get them to warm quicker. He knows Derek is waiting for him now. It takes forever for his hand to warm but when it doesn't feel so cold Stiles pulls it out and trails it back down to join Derek's hand around his cock.

He jerks Derek slow and relentlessly, just like Derek likes. When he comes he moans his orgasm into Stiles's neck, dropping his own hand and letting Stiles work him through the aftershocks.

When Derek's back to himself he kisses Stiles lazy and slow, and then jerks him off just the same. He even manages to get Stiles out of the stupid hoodie and sweatpants.

So alright, maybe they've not got fucking down to some fine art and occasionally they have what Stiles has termed 'sexual misadventures'.

But sometimes, sometimes they get it right... and it's fucking amazing.

**Author's Note:**

> [come and see me, make me smiiiiilllleee](http://saspiesas.tumblr.com/)


End file.
